Beta-halogenoethyl-silanes as plant growth regulators

ABSTRACT

The present invention relates to new compositions and methods for the regulation of plant growth, especially for fruit abscission, acceleration of ripening and latex discharge and to new active substances of the class of β-halogenoethyl-silanes. 
     The active substances in the new compositions respond to the formula ##STR1## wherein X is chlorine or bromine, Y represents chlorine or the radical --OR 3 , each of the radicals R 1 , R 2  and R 3  independently represent substituted or unsubstituted alkyl radicals, alkenyl, halogenalkenyl, alkynyl and cycloalkyl radicals, substituted or unsubstituted phenyl and benzyl radicals; one or more of the symbols R 1 , R 2  and R 3  can also represent the group --COR 4 , wherein R 4  stands for an unsubstituted or substituted alkyl or alkenyl radical, a possible phenyl substituent may itself be substituted or not, for an alkynyl, alkoxyalkyl, alkoxycarbonylalkyl, or phenyl radical optionally substituted or for a heterocyclic radical; R 1  and R 2 , also with the signification of --CO-R 4 , together with the adjacent atoms, can also form a silicium-containing saturated or unsaturated heterocyclic ring system. 
     The β-bromoethyl-silanes and the β-chloroethylsilanes of the above formula wherein R 1 , R 2 , R 3  and R 4  do not represent unsubstituted alkyl radicals with less than 6 carbon atoms, are new compounds.

Related Application

This is a division of application Ser. No. 443,180 filed on Feb. 15,1974, now U.S. Pat. No. 3,985,780, which in turn is acontinuation-in-part of Ser. No. 186,392, filed Oct. 4, 1971, nowabandoned.

Compounds which, under certain conditions, release ethylene are known.Such compounds are relatively unstable under the effects of weather,because they are very susceptible to hydrolysis; or they are phytotoxic.β-Halogen-ethyl-phosphonic acid derivatives are described in the SouthAfrican Patent No. 68/1036 as active substances regulating plant growth.These compounds decompose in and on the plant with the release ofethylene, and are therefore similar in action and range of action toethylene. By virtue of their very low stability, phosphonic acidderivatives are not able, however, to satisfy the demands made on them.As they are stable only in an acid medium, more precisely in a pH rangebelow 5, the active substance concentrates have to be stabilised by theaddition of acids. This acid addition limits, however, the range ofapplication of these active substances with regard to phytotoxiceffects. Furthermore, the storage of such sensitive active substanceconcentrates persents difficulties.

Also known, as herbicidal active substances, arehalogenalkyl-methyl-silanes, cp. U.S. Pat. Nos. 3,390,976 and 3,390,977,and J. K. Leasure et al., J. Med. Chem. 9, 949 (1966).β-Chloroethyl-tris-(alkoxy)-silanes and β-chloroethyl-acetoxy-dialkoxysilanes and β-chloroethyl-diacetoxy-alkoxy silanes have been produced byF. W. Boye et al., J. Org. Chem. 16, 391 (1951), resp. 17, 1386 (1952).

The U.S. Pat. No. 3,183,076 describesα-chloroethyl-methyldialkoxy-silanes, which can be used for thepromotion of germination power, leaf abscission, etc.

In contrast, the β-halogen-ethyl-silanes of this invention affect in avarying manner the growth of parts of plants situated above and belowthe ground; they are not phytotoxic in the usual concentrations in whichthey are applied, and have a low toxicity towards warm-blooded animals.The active substances produce no morphological changes or damage whichwould result in a withering of the plant. The compounds are notmutagenic. Their action differs from that of a herbicidal activesubstance and of a fertiliser. The action corresponds more to theeffects which can be observed on application of ethylene to variousparts of plants. It is known that also the plant itself produces, invarious stages of development, ethylene to a varying extent,particularly before and during the ripening process of the fruits, andat the end of the vegetation period as the abscission of the fruitoccurs. Since the regulation of fruit ripening and abscission bychemical substances is of the greatest commercial significance for thecultivation of fruit, citrus fruits, pineapples and cotton, compoundshave been sought with which such effects might be obtained withoutdamage being caused to the treated plants. Although various classes ofsubstances have become known with which it was possible for certain ofthese effects, with regard to growth regulation, to be achieved; thesphere of action of these substances in no way corresponds to that ofethylene.

The present invention relates to new agents and processes for theregulation of plant growth by the use of β-halogen-ethyl-silanes asactive substances, also to new β-halogen-ethyl-silanes, and to processesfor the production of these silanes.

The novel β-halogen-ethyl-silanes contained as active substances in thenew agents correspond to formula I: ##STR2## The symbols in this formulahave the following meanings: X represents chlorine or bromine, Yrepresents chlorine or the radical --OR₃ ; R₁, R₂ and R₃ represent,independently of each other, alkyl radicals having 6 to 18 carbon atoms;alkyl radicals substituted by halogen, alkoxy, alkenyloxy, phenoxy,cycloalkyl, alkylthio, alkoxycarbonyl, by a heterocyclic radical and/ordi- and trialkylammonio, alkenyl or halogenalkenyl; alkynyl; cycloalkyl;phenyl radicals optionally mono- or polysubstituted by cyano, alkyl,halogenalkyl, alkoxy, alkylthio, and/or alkoxycarbonyl; benzyl radicalsoptionally mono- or polysubstituted by alkyl, alkoxy and/or halogen; oneor more of the symbols R₁, R₂ and R₃ can also represent the group--CO--R₄ wherein R₄ stands for C₆ -C₁₈ alkyl, alkenyl or alkynylradical; a halogenalkyl or halogenalkenyl radical; an alkyl or alkenylradical substituted by cycloalkyl or phenyl, whereby phenyl can besubstituted by alkyl, alkoxy and/or halogen; an alkoxyalkyl; analkoxycarbonylalkyl; a phenyl radical optionally substituted by halogen,lower alkyl or lower alkoxy; or a heterocyclic 5- or 6-membered radical,R₁ and R₂, also with the signification of --CO--R₄, together with theadjacent atoms, can also form a silicium containing saturated orunsaturated heterocyclic ring system.

By alkyl radicals in formula I, other than when R₁, R₂, R₃ or R₄ isunsubstituted alkyl, are meant straight-chain or branched radicalshaving 1 to 18 carbon atoms, such as, e.g. methyl, ethyl, n-propyl,isopropyl, n-butyl, sec-butyl, n-hexyl, n-octyl, n-dodecyl, n-octadecyl,etc. Especially the straight-chain and branched alkyl radicals having 1to 8 carbon atoms form the alkyl substituents or the alkyl moiety ofalkoxy, alkylthio, di- and trialkylammonio or alkoxycarbonylsubstituents of an alkyl radical or of a phenyl radical. Halogenalkylradicals are alkyl radicals having 1 to 6 carbon atoms, which can besubstituted by fluorine, chlorine and/or bromine, such as, e.g.trifluoromethyl, 2-chloroethyl, 6-chlorohexyl, etc. By alkenyl radicalsare meant, in formula I, straight-chain or branched radicals having 3 to18 carbon atoms, e.g. propenyl, butenyl, octenyl, decenyl, heptadecenylradicals. These alkenyl radicals can be mono- or polysubstituted byhalogens, such as fluorine, chlorine, bromine and/or iodine. Alkenylradicals having 3 to 6 carbon atoms form the alkenyl moiety ofalkenyloxy radicals. Alkynyl radicals preferably contain 3 to 8 carbonatoms in a straight chain, such as, e.g. 2-propynyl, 2-butynyl or3-hexynyl. By cycloaliphatic radicals are meant mono- or polycycliccycloalkyl or cycloalkenyl radicals having 3 to 12 carbon atoms, suchas, e.g. cyclopropyl, cyclopentyl, cyclopentenyl, cyclohexyl,cyclohexenyl, bicycloheptyl, etc.

5- or 6-Membered heterocyclic radicals as R₄ or as substituents of alkylradicals R₁, R₂, R₃ may contain 1 or 2 hetero atoms, especially nitrogenand/or oxygen. Heterocyclic ring systems containing the Si-atom andbeing formed by radicals R₁ and R₂, including also the type --COR₄, maybe saturated or unsaturated, the bridging hydrocarbon moiety of R₁ + R₂being an alkylene or alkenylene member. Anions of di- or trialkylammonioradicals (which may be considered as salt forms of a dialkyl aminoradical) are e.g. those of hydrogen halides, hydrohalogenic acids, alkylsulfonic acids, alkyl phosphoric acids, and the like.

Preferred compounds correspond to the formulae ##STR3## wherein R₁, R₂and R₃ are identical and are defined as previously noted; and

    X -- CH.sub.2 -- CH.sub.2 -- Si -- (O--CO--R.sub.4).sub.3  (IB)

wherein X and R₄ are as previously defined.

Particularly preferred compounds of formula IA have R₁, R₂ and R₃represent alkyl of from 6 to 18 carbon atoms, halogenalkyl, alkenyl,halogenoalkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl and benzyloptionally substituted by alkyl, alkoxy or halogen; and, furthermore,where R₁, R₂ and R₃ represent alkyl of from 6 to 18 carbon atoms,halogenoalkyl, alkoxyalkyl, and alkylthioalkyl.

The new β-halogen-ethyl-silanes according to the present invention areproduced by reaction of a β-halogen-ethyl-trichlor-silane of formulaIII:

    x -- ch.sub.2 -- ch.sub.2 -- si -- (Cl).sub.3              (II)

with three equivalents of an acid of formula III: ##STR4## or of acarboxylic acid anhydride of formula IV: ##STR5## to give a compound offormula V: ##STR6## and, optionally, by stepwise exchange of one, two orthree of the radicals ##STR7## by radicals of alcohols of the formulaeVI, VII, VIII

    R.sub.1 OH                                                 (VI)

    r.sub.2 oh                                                 (vii)

    r.sub.3 oh                                                 (viii)

if, in the starting compound of formula II X represents bromine, alsolow molecular alkanols may be used for the exchange of the radicals--O--CO--R₄ in formula V. If no one of the radicals R₁, R₂ and R₃ isidentical with ##STR8## then the new β-halogen-ethyl-silanes of formulaeI can be produced according to a variant of the process by reaction of aβ-halogen-ethyl-trichloro-silane of formula II with one, two or threeequivalents of one of the alcohols of the formulae VI, VII or VIII.

X in formula II represents chlorine or bromine; R₄ in formulae III andIV has the meaning given under formula I; and R₁, R₂ and R₃ in formulaeVI, VII and VIII have the meaning given under formula I.

As in the reaction according to the invention, the exchange of the 3chlorine atoms of the starting compound of formula II occurs stepwise,it is clear that intermediates, i.e. dichloro- and monochloro-silanes offormulae ##STR9## can be isolated during the synthesis or as impuritiesfrom the crude final product.

The compounds (b) are embraced by the general formulae I and show alsobiological, plant growth regulating activity.

The process is preferably carried out in the presence of solvents and/ordiluents which are inert to the reactants. Aprotic solvents areparticularly suitable, such as, e.g. aliphatic and aromatichydrocarbons, e.g. hexane, cyclohexane, benzene, toluene, xylene,halogenated hydrocarbons such as chlorinated ethylene, carbontetrachloride, chloroform, chlorobenzene, also ethers and etherealcompounds such as diethyl ether, tetrahydrofuran, etc.

To obtain a complete reaction, it is also possible for the alcohols,carboxylic acids and carboxylic acid anhydrides employed as reactants toserve, when used in excess, as solvents or diluents.

Furthermore, it can be necessary in some cases to add an acid-bindingagent to the reaction mixture. Suitable for this purpose are, inparticular, tertiary amines such as trialkylamines, e.g. triethylamine,pyridine and pyridine bases, dialkylanilines, etc.

The reaction temperatures are in the range of 0° to 100° C; the reactionduration can be between a few minutes and several days, and depends to agreat extent on the reactivity of the alcohols employed.

The present invention also realates to new compositions containing, asactive substances, β-halogen-ethyl-silanes, the said new compositionshaving a stimulating or retarding effect on plant growth in the variousstages of development of the plants. By virtue of the very goodstability of the active substances of formula I, these compositions(agents) must not contain, apart from the usual carriers, distributingagents, and stabilisers protecting against the effects of light andoxidation, any additional acid stabilising additive, and have therefore,an unlimited field of application. The vegetative plant growth and thegermination power are influenced by the new agents; and the blossomformation, the development of the fruit and the formation of separatingtissues promoted. In the case of monocotyledons, an increase intillering and branching was observed with a simultaneous reduction ofgrowth in height. There was moreover a strengthening of the supporttissues of the stalks in the case of the treated plants. The formationof undesirable side shoots is very greatly reduced on various types ofplants. Furthermore, gum trees are stimulated to produce a greater latexdischarge, an effect which is of great commercial importance. A controlof the blossoming time and of the number of blossoms is possible in thecase of many ornamental and cultivated plants. This effect is anespecially important factor in connection with pineapples. If all thetrees or shrubs blossom simultaneously, then the crops can be gatheredwithin a comparatively short space of time. With regard tocucurbitaceae, there occurs a displacement of the blossom sexdifferentiation in favour of pistillate flowers.

The active substances promote the development of abscission layers,particularly between stalks and petioles. Consequently, fruits of allkinds, e.g. apples, pears, peaches, tomatoes, bananas, prunes,pineapples, cherries, citrus fruits and, particularly oil fruits(olives) can be separated from the fruit stems manually or mechanicallywithout the exertion of great force. It is particularly in the area ofolive abscission that the instant compounds excel. Damage to foliage andbranches, which results from shaking trees and shrubs or by pluckingfruit is largely avoided and production capacity increased. Tests havealso shown that in the case of fruit trees, particularly peaches, thereoccurs a thinning of blossom and fruit.

The extent and the nature of the action are dependent on the mostdiverse factors, particularly on the time of application with regard tothe stage of development of the plant, and on the applicationconcentration. These factors vary, however, depending on the type ofplant and on the desired effect. Thus, for example, ornamental plants,of which, e.g. the intensity and number of the blossoms are to beincreased, before development of the blossom setting; plants of whichthe fruit is to be sold, or in some other way utilized, after blossomingor at an appropriate interval of time before the gathering of the crop.Application of the active substances is effected by the use of solid orliquid agents, these being applied to parts of plants above the ground,to the surface of the soil, as well as into the soil itself. Thepreferred method is the application to the parts of plants above thesoil, for which purpose solutions or aqueous suspensions are mostsuitable. In addition to solutions and dispersions for the treatment ofthe growth substrate (soil), dusts, granulates and scattering agents arealso suitable.

The plant growth regulating action of the new agents can often bepositively influenced by the addition of organic or inorganic acids andbases (e.g. acetic acid or sodium carbonate).

Agents according to the invention are produced in a manner known per seby the intimate mixing and grinding of active substances of the generalformula I with suitable carriers, optionally with the addition ofdispersing agents or solvents which are inert to the active substances.

Water-dispersible concentrates of active substance, i.e. wettablepowders, pastes and emulsion concentrates, are active substanceconcentrates which can be ciluted with water to obtain any desiredconcentration. They consist of active substances, carrier, optionallyadditives which stabilize the active substance, surface-activesubstances, and anti-foam agents and, optionally, solvents. Theconcentration of active substance in these agents is 0.5 - 80%.

The wettable powders and pastes are obtained by the mixing and grindingof the active substances with dispersing agents and pulverulentcarriers, in suitable devices, until homogeneity is attained. Suitablecarriers are, e.g. the following: kaolin, talcum, bole, loess, chalk,limestone, ground limestone, Attaclay, dolomite, diatomaceous earth,precipitated silicic acid, alkaline-earth silicates, sodium andpotassium aluminium silicates (feldspar and mica), calcium and magnesiumsulphates, magnesium oxide, ground synthetic materials, fertilisers suchas ammonium sulphate, ammonium phosphate, ammonium nitrate, urea, groundvegetable products such as bran, bark dust, sawdust, ground nutshells,cellulose powder, residues of plant extractions, active charcoal, etc.,alone or in admixture with each other.

Suitable dispersing agents are, e.g. the following: condensationproducts of sulphonated naphthalene and sulphonated naphthalenederivatives with formaldehyde, condensation products of naphthalene orof naphthalene-sulphonic acids with phenol and formaldehyde, as well asalkali, ammonium and alkaline-earth metal salts of ligninsulphonic acid,also alkylarylsulphonates, alkali metal salts and alkaline-earth metalsalts of dibutylnaphthalenesulphonic acid, fatty alcohol sulphates suchas salts of sulphated hexadecanols, heptadecanols, octadecanols, andsalts of sulphated fatty alcohol glycol ether, the sodium salt of oleylmethyl tauride, ditertiary acetylene glycols, dialkyl dilauryl ammoniumchloride, and fatty acid alkali-metal and alkaline-earth metal salts.

To these mixtures may also be added additives stabilizing the activesubstance, and/or non-ionic, anion-octive and cation-active substances,which, for example, improve the adhesiveness of the active substances onplants and on parts of plants (adhesives and agglutinants), and/orensure a bettwe wettability (wetting agents). Suitable adhesives are,for example, the following: olein/lime mixture, cellulose derivatives(methyl cellulose, carboxymethyl cellulose), hydroxyethylene glycolethers of mono- and dialkylphenols having 5 - 15 ethylene oxide radicalsper molecule and 8 - 9 carbon atoms in the alkyl radical,ligninsulphonic acid, alkali metal and alkaline-earth metal saltsthereof, polyethylene glycol ethers (carbowaxes), fatty alcoholpolyglycol ethers having 5 - 20 ethylene oxide radicals per molecule and8 to 18 carbon atoms in the fatty alcohol moiety, condensation productsof ethylene oxide, propylene oxide,, polyvinylpyrrolidones, polyvinylalcohols, condensation products of urea/formaldehyde, as well as latexproducts. The active substances are so mixed, ground, sieved andstrained with the above-mentioned additives that the solid constituentin the case of wettable powders has a particle size not exceeding 0.02to 0.04 mm, and in the case of pastes not exceeding 0.03 mm.

Emulsion concentrates and pastes are prepared by application of thedispersing agents such as those mentioned in the preceding paragraphs,organic solvents and water. Suitable solvents are, e.g. the following:ketones, benzene, xylenes, toluene, dimethylsulphoxide, and mineral oilfractions boiling in the range of 120° to 350°. The solvents must bepractically odourless, non-phytotoxic, and inert to the activesubstances.

Furthermore, the agents according to the invention can be employed inthe form of solutions. For this purpose, the active substance (orseveral active substances) of the general formula I is (or are)dissolved in suitable organic solvents, solvent mixtures, or water. Thefollowing can be used as organic solvents: aliphatic and aromatichydrocarbons, chlorinated derivatives thereof, alkylnaphthalenes, ormineral oils on their own or in admixture with each other. The solutionsshould contain the active substances in a concentration range of from 1to 20%.

The solid preparations, such as dusts, scattering agents and granulates,contain aolid carriers such as those mentioned in the foregoing, and,optionally, additives stabilizing the active substance. The particlesize of the carriers is for dusts advantageously up to about 0.1 mm; forscattering agents from about 0.075 mm to 0.2 mm; and for granulates 0.2mm or coarser. The concentrations of active substance in the solidpreparations are from 0.5 to 80%.

All the mentioned active substance concentrates may also contain agentsstabilizing against the effects of light, and antioxidants.

GRANULATE

The following substances are used for the preparation of a 5% granulate:

5 parts of 2-chloroethyl-tris-(2'-chloroethoxy)-silane,

0.25 parts of epichlorohydrin,

0.25 parts of cetyl polyglycol ether,

3.50 parts of polyethylene glycol ("carbowax"),

91 parts of kaolin (particle size 0.2 - 0.8 mm).

The active substance is mixed with epichlorohydrin and the mixturedissolved in 6 parts of acetone; to the solution are then addedpolyethylene glycol and cetyl polyglycol ether. The thus obtainedsolution is sprayed on to kaolin, and the acetone subsequentlyevaporated in vacuo.

WETTABLE POWDER

The following constituents are used for the preparation of a) a 40%, b)a 50%, c) a 25%, and d) a 10% wettable powder:

(a)

40 parts of 2-chloroethyl-tris-(octyloxy)-silane,

5 parts of sodium lignin sulphonate,

1 part of sodium dibutyl-naphthalene sulphonate,

54 parts of silicic acid;

(b)

50 parts of 2-chloroethyl-tris-(dodecyloxy)-silane,

5 parts of alkylaryl sulphonate ("Tinovetin B"),

10 parts of calcium lignin sulphonate,

1 part of Champagne chalk/hydroxyethyl cellulose mixture (1:1),

20 parts of silicic acid,

14 parts of kaolin;

(c)

25 parts of 2-chloroethyl-tris-(4'-methoxy-benzoxy)-silane,

5 parts of the sodium salt of oleylmethyl tauride,

2.5 parts of naphthalenesulphonic acid/formaldehyde condensate,

0.5 parts of carboxymethyl cellulose,

5 parts of neutral potassium aluminium silicate.

62 parts of kaolin;

(d)

10 parts of 2-chloroethyl-tris-(4'-chlorobenzoxy)-silane,

3 parts of a mixture of the sodium salts of saturated fatty alcoholsulphates,

5 parts of naphthalenesulphonic acid/formaldehyde condensate,

82 parts of kaolin.

The active substances are intimately mixed, in suitable mixers, with theadditives; the mixture is subsequently ground in suitable mills androllers. Wettable powders are thus obtained which can be diluted withwater to give suspensions of any desired concentration.

EMULSION CONCENTRATE

The following constituents are mixed together to produce 25% emulsionconcentrates:

(a)

25 parts of 2-chloroethyl-tris-(benzoxy)-silane,

5 parts of a mixture of nonylphenolpolyoxyethylene andcalcium-dodecylbenzene sulphonate,

70 parts of xylene;

(b)

25 parts of 2-chloroethyl-tris-(2'-chloroethoxy)-silane,

10 parts of a mixture of nonylphenolpolyoxyethylene andcalcium-dodecylbenzene sulphonate,

65 parts of cyclohexanone.

This concentrate can be diluted with water to obtain emulsions of anydesired concentration. Such emulsions are suitable for the thinning outof blossom and fruit, for the accelerated ripening of fruits, and forthe promotion of fruit and leaf abscission.

The following examples serve to illustrate the preparation of thecompounds of this invention. Listed in the attached tables are furthernew β-halogen-ethyl-silanes of formulae I and II produced in the mannerdescribed in the examples.

The temperatures are given in the examples in degrees Centigrade, andthe pressure in Torr.

EXAMPLE 1

(a) An amount of 40.8 g of 2-chloroethyl-trichlorosilane is dissolved in71.5 g of acetic acid anhydride, and the solution allowed to stand atroom temperature for 21 hours in a closed vessel. The reaction productis concentrated in vacuo to obtain 44.6 g of2-chloro-ethyl-tris-(acetyloxy)-silane, B.P.: 85° - 88°/0.1 Torr, n_(D)²⁰ = 1.6687.

(b) An amount of 26.9 g of 2-chloroethyl-tris-(acetyloxy)-silane isdissolved in 40 ml of absolute benzene. To the solution are added at50° - 55°, within 60 minutes, 10.8 g of benzyl alcohol in 20 ml ofabsolute benzene. Stirring is carried out for 41/2 hours at 50° - 55°.The reaction mixture is concentrated in vacuo, and 14.3 g of2-chloroethyl-(benzyloxy-diacetyloxy)-silane are obtained, B.P.: 125° -127°/0.001 Torr, n_(D) ²⁰ = 1.4840. (Compound 1).

    ______________________________________                                                  Calculated  Found                                                   ______________________________________                                        C           49.3          49.4                                                H           5.4           5.4                                                 Cl          11.2          11.7                                                Si          8.9           8.9                                                 ______________________________________                                    

EXAMPLE 2

An amount of 26.9 g of 2-chloroethyl-tris-(acetyloxy)-silane, obtainedaccording to example 1a, is dissolved in 40 ml of absolute benzene; tothis solution are then added at 50° - 55°, within 60 minutes, 21.6 g ofbenzyl alcohol in 20 ml of absolute benzene. Stirring is carried out for41/2 hours at 50° - 55°. The reaction mixture is concentrated in vacuoto obtain 20.2 g of 2-chloroethyl-(dibenzyloxy-acetyloxy)-silane, B.P.:164° - 166°/0.005 Torr, n_(D) ²⁵ = 1.5218. (Compound 2).

    ______________________________________                                                  Calculated  Found                                                   ______________________________________                                        C           59.3          59.4                                                H           5.8           5.6                                                 Cl          9.7           10.2                                                Si          7.7           8.0                                                 ______________________________________                                    

EXAMPLE 3

An amount of 10.5 g of 2-chloroethyl-trichlorosilane is dissolved in 150ml of absolute diethyl ether; to this solution are then added at -5° to-10°, within 5 minutes, 22.7 g of 4-chlorobenzyl alcohol, and followingthis, in the course of 30 minutes, 12.6 g of absolute pyridine dissolvedin 50 ml of absolute ether. Stirring is carried out for a further hourat 0°, and the mixture then refluxed for 18 hours.

The reaction mixture is filtered, the filtrate washed twice with water,dried, and concentrated in vacuo. In this manner are obtained 23.5 g of2-chloroethyl-tris-(4'-chlorobenzoxy)-silane, B.P.: 200° - 210°/0.01Torr, n₂₀ ^(D) = 1.5636. (Compound 3).

    ______________________________________                                                  Calculated  Found                                                   ______________________________________                                        C           53.5          53.4                                                H           4.3           4.3                                                 Cl          27.5          27.8                                                Si          5.4           5.6                                                 ______________________________________                                    

EXAMPLE 4

An amount of 16.9 g of 3-chlorobuten-(2)-ol is dissolved in 150 ml ofabsolute diethyl ether. The solution is cooled to -10° to -5° and 12.6 gof absolute pyridine are added; at the same temperature is then addeddropwise, within one hour, a solution of 10.5 g of2-chloroethyltrichlorosilane in 50 ml of absolute diethyl ether. Themixture is stirred for one hour at 0°, for 2 hours at room temperature,and for 18 hours with refluxing. The reaction mixture is afterwardsfiltered, the filtate quickly washed with ice-cold water, dried, andconcentrated in vacuo. Thus obtained are 21.5 g of2-chloroethyl-tris-[3'-chlorobutenyl-(2')-oxy]-silane, B.P.: 145° -150°/0.05 Torr, n₂₀ ^(D) = 1.4912. (Compound 4).

    ______________________________________                                                  Calculated  Found                                                   ______________________________________                                        C           41.2          41.6                                                H           5.4           5.4                                                 Cl          34.8          34.9                                                Si          6.9           6.6                                                 ______________________________________                                    

EXAMPLE 5 (Production of an intermediary product)

An amount of 59.4 g of 2-chloroethyl-trichloro-silane is dissolved in750 ml of absolute diethylether. To the obtained solution is then addedat -5° to -10°, within 1 hour, a solution of 34.9 g of hexanol-(1) and23.7 g of absolute pyridine in 250 ml of absolute diethylether. Themixture is then stirred for 12 hours at room temperature, filtered andthe filtrate concentrated by evaporation in vacuo. After fractionateddistillation, 39.2 g of 2-chloroethyl-(hexyloxy-dichloro)-silane areobtained; B.P.: 69°-72°/0.1 Torr.

    ______________________________________                                                  Calculated  Found                                                   ______________________________________                                        C           36.5          36.3                                                H           6.5           6.5                                                 Si          10.7          11.0                                                ______________________________________                                    

EXAMPLE 6

An amount of 59.4 g of 2-chloroethyl-trichloro-silane is dissolved in750 ml of absolute diethylether. To the obtained solution is then addedat -5° to -10°, within 1 hour, a solution of 69.7 g hexanol-(1) and 47.5g absolute pyridine in 250 ml of absolute diethylether. The mixture isthen stirred for 12 hours at room temperature, filtered and the filtrateconcentrated by evaporation in vacuo. After fractionated distillation,32.5 g of 2-chloro-(dihexyloxy-chloro)-silane are obtained; B.P.:97°-102°/0.001 Torr; n_(D) ²⁰ = 1.4423. (Compound 5).

                  Table I                                                         ______________________________________                                        Compounds of formula                                                           ##STR10##                                                                                                 Physical data                                    No.  R.sub.1 = R.sub.2 = R.sub.3                                                                     X     M.P.; B.P./Torr; n.sub.D                         ______________________________________                                         6   Hexyl             Br    B.P.: 145-50°/0,01                         7   2-Ethyl-hexyl     Cl    n.sub.D.sup.20 = 1,4480                           8   Octyl             Cl    B.P.: 165-70°/0,001                        9   Octyl             Br    B.P.: 165-70°/0,005                       10   Dodecyl           Cl    n.sub.D.sup.20 = 1,4545                          11   Dodecyl           Br    n.sub.D.sup.20 = 1,4582                          12   Octadecyl         Cl    M.P.: 33-36°                              13   Octadecyl         Br    M.P.: 35-36°                              14   2-Chloroethyl     Cl    B.P.: 123-26°/0,001                       15   2-Chloropropyl    Cl    B.P.: 128°/0,001                          16   6-Chlorohexyl     Cl    B.P.: 210-15°/0,03                        17   2-Methoxyethyl    Cl    B.P.: 103-105°/0,05                       18   2-Ethoxyethyl     Cl    B.P.: 122-125°/0,005                      19   2-Ethoxyethyl     Br    B.P.: 173°/0,001                          20   2-Butyloxyethyl   Cl    n.sub.D.sup.20 = 1,4495                          21   2-Allyloxyethyl   Cl    B.P.: 140-145°/0,001                      22   2-Ethylthioethyl  Cl    B.P.: 195-200°/0,005                      23   2-Octylthioethyl  Cl    n.sub.D.sup.20  = 1,4895                         24   3-Phenylpropyl    Cl    n.sub.D.sup.20 = 1,5340                          25   2-Phenoxyethyl    Cl    n.sub.D.sup.20 = 1,5466                          26   2-Propenyl        Cl    B.P.: 95-100°/0,2                         27   2-Butenyl         Cl    B.P.: 110-15°/0,2                         28   2-Butenyl         Br    B.P.: 115-20°/0,01                        29   3,7-Dimethyl-2-octe-                                                          nyl               Cl    n.sub.D.sup.20 = 1,4707                          30   2-Propinyl        Cl    B.P.: 94°/0,35                            31   2-Propinyl        Br    B.P.: 115-20°/0,005                       32   3-Hexinyl         Cl    B.P.: 170-5°/0,005                        33   3-Chloro-2-butenyl                                                                              Cl    B.P.: 145-50°/0,005                       34   3-Phenyl-2-propenyl                                                                             Cl    n.sub.D.sup.20 = 1,5832                          35   3-Phenyl-2-propenyl                                                                             Br    n.sub.D.sup.20 = 1,5882                          36   3-Cyanoethyl      Cl    n.sub.D.sup.20 = 1,4969                          37   Ethoxycarbonyl- - methyl                                                                              Cl n.sub.D.sup.20 = 1,4496                       38   1-Ethoxycarbonyl- Cl    B.P.: 154-158°/0,3                             (1-methyl)-methyl                                                        39   Butoxycarbonyl-   Cl    n.sub.D.sup.20 = 1,4480                               methyl                                                                   40   Cyclohexyl        Cl    B.P.: 165-170°/0,001                      41   Cyclohexylmethyl  Cl    B.P.: 180-190°/0,001                      42   Cyclohexylmethyl  Br    n.sub.D.sup.20 = 1,4833                          43   Benzyl            Cl    B.P.: 190-200°/0,001                      44   Benzyl            Br    n.sub.D.sup.20 = 1,5612                          45   4-Chlorobenzyl    Cl    B.P.: 200-20°/0,01                        46   4-Chlorobenzyl    Br    n.sub.D.sup.20 = 1,5757                          47   4-Methoxybenzyl   Cl    n.sub.D.sup.20 = 1,5224                          48   2,4-Dichlorobenzyl                                                                              Cl    n.sub.D.sup.20 = 1,6637                          49   4-Methylbenzyl    Cl    n.sub.D.sup.20 = 1,5433                          50   Phenyl            Cl    n.sub.D.sup.20 = 1,5623                          51   4-Chlorophenyl    Cl    n.sub.D.sup.20 = 1,5769                          52   3-Chlorophenyl    Cl    n.sub.D.sup.27 = 1,5262                          53   3,4-Dichlorophenyl                                                                              Cl    n.sub.D.sup.27 = 1,5257                          54   3,5-Dichlorophenyl                                                                              Cl    n.sub.D.sup. 20 = 1,5268                         55   4-Bromophenyl     Cl    n.sub.D.sup.27 = 1,5418                          56   4-Methoxyphenyl   Cl    n.sub.D.sup.20 = 1,5620                          57   4-Methoxyphenyl   Br    n.sub.D.sup.20 = 1,5641                          58   3-Methoxyphenyl   Cl    n.sub.D.sup.20 = 1,5590                          59   4-Butyloxyphenyl  Cl    n.sub.D.sup.20 = 1,5307                          60   4-tert-Butylphenyl                                                                              Cl    M.P.: 75-77°                              61   3-Methylphenyl    Cl    n.sub.D.sup.27 = 1,5385                          62   3-Methylphenyl    Br    n.sub.D.sup.20 = 1,5490                          63   3,4-Dimethylphenyl                                                                              Cl    n.sub.D.sup.27 = 1,4935                          64   3-Formylphenyl    Cl    M.P.: 98-101°                             65   4-Cyanophenyl     Cl    M.P.: 106-111°                            66   4-Ethoxycarbonylphenyl                                                                          Cl    M.P.: 112-114°                            67   3-Ethoxycarbonylphenyl                                                                          Cl    M.P.: 65-70°                              68                                                                                  ##STR11##        Cl    B.P.: 195-200°/0,001                      69                                                                                  ##STR12##        Cl    B.P.: 152-154°/0,001                      70                                                                                  ##STR13##        Cl    n.sub.D.sup.23 = 1,5771                          71                                                                                  ##STR14##        Cl    n.sub.D.sup.25 = 1,4727                          ______________________________________                                    

                  Table II                                                        ______________________________________                                              R.sub.1 = R.sub.2 = R.sub.3 =COR.sub.4                                  No.   R.sub.4 is:         X     Physical data                                 ______________________________________                                        72    Undecyl             Cl    M.P.: 42-44°                           73    Undecyl             Br    M.P.: 44-47°                           74    Heptadecyl          Cl    M.P.: 54-57°                           75    2-Propenyl          Cl    n.sub.D.sup.20 = 1,4484                       76    1-Propenyl          Cl    M.P.: 24-27°                           77    2-Propenyl          Br    n.sub.D.sup.20 = 1,4621                       78    9-Decenyl           Cl    n.sub.D.sup.20 = 1,4480                       79    8,11-Heptadecadienyl                                                                              Cl    n.sub.D.sup.20 = 1,4705                       80    2-Chloroethyl       Cl    n.sub.D.sup.20 = 1,4681                       81    1-Bromppentyl       Cl    n.sub.D.sup.20 = 1,4513                       82    10-Bromodecyl       Cl    M.P.: 49-50°                           83    10-Bromodecyl       Br    M.P.: 48-50°                           84    cis-2-Chloroethenyl Cl    M.P.: 25°                              85    cis-2-Chloroethynyl Br    M.P.: 55-58°                           86    Phenylmethyl        Cl    M.P.: 75-78°                           87    Phenylmethyl        Br    M.P.: 20-30°                           88    2-Phenylethyl       Cl    M.P.: 35-39°                           89    4-Chlorphenylmethyl Cl    M.P.: 99-103°                          90    3-Methylphenylmethyl                                                                              Cl    M.P.: 67-60°                           91    3-(4'-Methoxyphenyl)-ethyl                                                                        Cl    M.P.: 98-102°                          92    4-Ethoxycarbonylbutyl                                                                             Cl                                                  93    3-Oxobutyl          Cl    n.sub.D.sup.20 = 1,4590                       94    3-Oxobutyl          Br    n.sub.D.sup.20 = 1,4841                       95    5-Phenyl-5-oxo-pentyl                                                                             Cl    M.P.: 75-75°                           96    2-Ethoxyethyl       Cl    n.sub.D.sup.20 = 1,4365                       97    3-Phenoxypropyl     Cl    M.P.: 58.60°                           98    2,4-Dichlorophenoxymethyl                                                                         Cl    M.P.: 140°                             99    2,4-Dichlorophenoxymethyl                                                                         Br    M.P.: 137-138°                         100   2-(4'-Chlorphenyl)-1-ethenyl                                                                      Cl                                                  101   2-Phenyl-1-ethenyl  Cl    M.P.: 128-130°                         102   2-Phenyl-1-ethenyl  Br    M.P.: 129-131°                         103   2-(3',4'-Dichlor henyl)-1-                                                    ethenyl             Cl    M.P.: >235°                            104   2-(4'-Methoxyphenyl-1-ethenyl                                                                     Cl    M.P.: 178°                             105   Cyclohexylmethyl    Cl    n.sub.D.sup.20 = 1,4494                       106   Cyclohexylmethyl    Br    n.sub.D.sup.20 = 1,4592                       107   Cyclohexyl          Cl    n.sub.D.sup.20 = 1,4578                       108   Cyclopropyl         Cl    n.sub.D.sup.20 = 1,4515                       109   3-Cyclohexenyl      Cl    n.sub.D.sup.20 = 1,4740                       110   3-Cyclohexenyl      Br    n.sub.D.sup.20 = 1,4807                       111   2-Cyclopentenyl     Cl    n.sub.D.sup.20 = 1,4680                       112   2-Cyclopentenyl     Br                                                  113   Phenyl              Cl    n.sub.D.sup.20 = 1,5632                       114   4-Chlorophenyl      Br    M.P.: 233°                             115   4-Methoxy-phenyl    Br    M.P.: 177-178°                         116   4-Methylphenyl      Cl    M.P.: 165-170°                         117                                                                                  ##STR15##          Br                                                  118                                                                                  ##STR16##          Br    M.P.: 123-126°                         119                                                                                  ##STR17##          Br    M.P.: 123-125°                         120                                                                                  ##STR18##          Cl                                                  ______________________________________                                    

                  Table III                                                       ______________________________________                                                                R.sub.3 =                                                                     CO--R.sub.4                                           No.  R.sub.1   R.sub.2  R.sub.4 is:                                                                          X   Physical data                              ______________________________________                                        121  Benzyl    = R.sub.3                                                                              Methyl Cl  B.P.: 126-27°/0,001                 122  Benzyl    = R.sub.3                                                                              Methyl Br  B.P.:140-143°/0,01                  123  Benzyl    Benzyl   Methyl Cl  B.P.: 164-166°/0,005                124  Octyl     = R.sub.3                                                                              Methyl Cl  B.P.: 115-120°/0,02                 125  Octyl     Octyl    Methyl Cl  B.P.: 150-152°/0,005                126  2-Butynyl 2-       Methyl Cl                                                            Butynyl                                                        127  2-Butenyl 2-       Methyl Cl  B.P.: 94-98°/0,001                                 Butenyl                                                        128  4-Chlor                                                                       benzyl    = R.sub.3                                                                              Ethyl  Cl  n.sub.D.sup.20 = 1,4940                    129  4-Chlor                                                                       benzyl    = R.sub.3                                                                              Ethyl  Br  n.sub.D.sup.20 = 1,5042                    130  3,7-Dime-                                                                     thyl-7-                                                                       octenyl   = R.sub.3                                                                              Ethyl  Cl  n.sub.D.sup.20 = 1,4525                    131  4-Methoxy-                                                                    benzyl    = R.sub.3                                                                              Ethyl  Cl  n.sub.D.sup.20 = 1,4890                    ______________________________________                                    

                                      Table IV                                    __________________________________________________________________________                                      physical                                    No. R.sub.1       R.sub.2                                                                            R.sub.3                                                                            X anion                                                                             data                                        __________________________________________________________________________    132                                                                                ##STR19##    Hexyl                                                                              Hexyl                                                                              Cl                                                                              Cl.sup.⊖                                                                  M.P.:25-35°                          133                                                                                ##STR20##    Benzyl                                                                             Benzyl                                                                             Cl                                                                              Cl.sup.⊖                                                                  n.sub.D.sup.20 = 1,5212                     __________________________________________________________________________

                  Table V                                                         ______________________________________                                        (Compounds wherein R.sub.1 and R.sub.2, together with the adjacent            atoms, form a Si-containing heterocyclic ring system).                        No.  active substance        Physical data                                    ______________________________________                                        134                                                                                 ##STR21##              B.P.: 115-120°/ 0,005                     135                                                                                 ##STR22##              n.sub.D.sup.25 = 1,5233                          136                                                                                 ##STR23##              n.sub.D.sup.20 = 1,4718                          137                                                                                 ##STR24##              n.sub.D.sup.20 = 1,4537                          138                                                                                 ##STR25##              n.sub.D.sup.20 = 1,4400                          139                                                                                 ##STR26##              n.sub.D.sup.25 = 1,4502                          ______________________________________                                    

PERFORMANCE CHARACTERISTICS Orange Abscission

It was determined in the case of citrus fruits - oranges - that theabscission of fruit is appreciably easier after application of theactive substances of formula I. Various active substances were sprayed,in the form of solutions in concentrations of 0.2% - 0.4%, on tobranches, well hung with fruit, of various orange trees. The tests wereevaluated after 14 days according to the method developed by W. C.Wilson and C. H. Hendershott, cp. Proc. Am. Soc. Hort. Sc. 90, 123-129(1967). The test consists of measuring the force in kg required for theabscission of the fruit.

    ______________________________________                                        Active substance:                                                                           Concentration Force (kg)                                        ______________________________________                                         8            0.2%          3.7                                                             0.4%          *                                                 43            0.2 %         *                                                               0.4 %         *                                                 10            0.2 %         4.7                                                             0.4 %         1.1                                               Control                     8.6                                               ______________________________________                                         *The fruit hanging on the tree could be so easily detached that no            measurement was possible.                                                

Equally good and significant results were obtained using agentscontaining the following compounds:

2-chloroethyl-tris-(2'-chloroethoxy)-silane,

2-chloroethyl-tris-[butenyl-(2')-oxy]-silane,

2-chloroethyl-tris-[propenyl-(2')-oxy]-silane,

2-chloroethyl-tris-[3'-chlorobutenyl-(2')-oxy]-silane,

2-chloroethyl-tris-(octadecyloxy)-silane,

2-chloroethyl-tris-[butynyl-(2')-oxy]-silane,

2-chloroethyl-tris-[hexynyl-(3')-oxy]-silane,

2-chloroethyl-tris-(6'-chlorohexyloxy)-silane,

2-chloroethyl-tris-(4'-methoxy-benzoxy)-silane,

2-chloroethyl-tris-(2',4'-dichlorobenzoxy)-silane,

2-chloroethyl-tris-(4'-chlorobenzoxy)-silane.

Apple and Prune Abscission

A similar test procedure was conducted on apples and prunes by neasuringthe force in ounces required for the abscission thereof.

    ______________________________________                                        Active Substance                                                                           Concentration (ppm)                                                                          Pull Force (oz.)                                  ______________________________________                                        Apples                                                                               17         500           91.2                                                 17        1000           16.80                                                17        2000           11.84                                                17        4000           35.36                                                Control   --             106.88                                        Prunes                                                                               17        2000           30.75                                                Control   --             49.7                                          ______________________________________                                    

Tomato Ripening

Tomato plants of the variety "Fournaise" were cultivated outdoors underplastic sheets. After reaching a height of 1.5 m., the shoot tips of theplants were cut away. As the first fruits turn red the plants weresprayed with aqueous preperations formulated from emulsion concentratesof the under-mentioned active substances. Four plants were each treatedwith 1.5 l of a spray containing 2000 or 4000 ppm of active substance(ppm = parts active substance per million parts of solution). 10,14 and17 days after treatment the ripe fruits on the three lowest umbels wereharvested.

The sum of the yields (tomatoes) thus obtained is given in the followingtable:

    ______________________________________                                                          Yield of ripe fruits from                                             quantity                                                                              the ghree harvests                                                      employed              % of total                                  Active substance                                                                          (ppm)     weight in kg                                                                              harvest                                     ______________________________________                                         8          2000      4.05        61.2                                                    4000      5.76        71.5                                        43          2000      5.66        73.7                                                    4000      6.26        75.9                                        33          2000      5.92        85.2                                                    4000      6.50        84.3                                        27          2000      5.03        63.4                                                    4000      6.06        75.3                                        47          2000      5.50        70.6                                                    4000      7.30        87.7                                        45          2000      3.37        62.9                                                    4000      6.80        82.4                                        32          2000      5.32        77.7                                                    4000      5.94        85.2                                        untreated control     3.41        52.0                                        ______________________________________                                    

Immersion test with plucked green greenhouse tomatoes of the variety"Hybrid."

The active substances were prepared, in a concentration of 1000 and 2000ppm, as an aqueous liquor with an addition of wetting agent. Each testwas carried out with 2 liters of this liquor and 40 unripe pickedtomatoes, the procedure being that the tomatoes were immersed for 1minute in the liquor, and then stored in an air-conditioned room with70% rel. humidity and at 20° C, with a daily 10-hours' exposure to light(20,000) Lux). Relative degree of ripeness was determined after a periodof 7 days.

    ______________________________________                                                 Concen-                                                              Active   tration  Number of Tomatoes                                          Substance                                                                              (ppm)    Green   Breaking                                                                             Pink Orange                                                                              Red                               ______________________________________                                          17     1000     2       6      9    12    11                                  17     2000     3       4      5    10    16                                Untreated                                                                              --       7       3      10   11    9                                 Control                                                                       ______________________________________                                    

Latex Discharge

The resin flow comparable with the latex discharge of gum trees wasevaluated with damson trees in the following manner:

Segments of the bark were cut out from the boughs of 12 year old damsontrees (Prunus domestica). A 10% active substance solution (10 partsactive substance, 20 parts xylene, 70 parts castor oil) was then appliedto the undamaged surface of the boughs just above and below theabove-mentioned incisions, each treatment being repeated on 4 differenttrees.

Four weeks after said treatment the exuded resin was removed andweighed. The following table gives the average weight of collected resinper treated bough in grams.

    ______________________________________                                        Active substance      Grams resin                                             ______________________________________                                        56                    1.81                                                    31                    0.53                                                    45                    0.52                                                    32                    0.85                                                    control (untreated)   0                                                       ______________________________________                                    

Peach Thinning

Peach trees, or branches thereof, the variety "Elberta" and "FayElberta" were sprayed, subsequent to blossom fall, with aqueouscompositions of varying concentrations of active substance. At the timeof application, the young fruit was counted. Count was also taken atvarying intervals thereafter to determine the amount of remaining fruit.In addition, the remaining fruit was categorized into size with "E"representing the smallest, most undesirable fruit, "A" the largest fruitand "B" the most desirable, marketable fruit.

    ______________________________________                                        Fay Elberta Peaches (Branch Test)                                             ______________________________________                                                Rate    % Fruit   Average No.                                         Compound                                                                              (ppm)   Remaining Per Size Category                                   ______________________________________                                                        (56 Days) A    B    C    D    E                               17      1000    38        --   --   --   --   --                              17      1500    45        --   --   --   --   --                              17      2000    19        0    11   11   0    0                               22      1000    30        3    10   21   4    0                               22      1500    26        0    18    7   1    0                               22      2000    19        4    13    4   0    0                               Fay Elberta Peaches (Whole Tree Test)                                         ______________________________________                                        17      1000    44        --   --   --   --   --                              17      1500    29        --   --   --   --   --                              17      2000    34        2    17   18    3   0                               Control --      54        0     1   13   15   7                               Elberta Peaches (Branch Test)                                                 ______________________________________                                        Compound    Rate (ppm)    % Fruit Drop                                        ______________________________________                                                                  (28 days)                                           17          1000          76                                                  17          1500          86                                                  17          2000          90                                                  22          1000          99                                                  22          1500          98                                                  22          2000          100                                                 Control     --            76                                                  ______________________________________                                    

Olive Abscission

On olive trees of the varieties "Coratine," "Zorzalena" and"Hojiblanca," a large number of branches were sprayed, about 1 weekbefore the expected harvest of the olives, with aqueous compositions ofthe listed active ingredients. The concentration of the activeingredients in the spray liquid was always 2000 ppm. On each tree, somebranches were not treated and served as control branches. The tests wereevaluated 4 to 14 days after treatment, by uniformly shaking the treatedand untreated branches by hand. The olives which fell were counted, theresults given in the following table indicating the percent of fallenolives with respect to the initial number of olives on the correspondingbranches.

Similar test procedures were also conducted utilizing the followingprior art compounds of the aforementioned Leasure patents.

A-bromoethyl-dimethoxy-methyl silane

B-chloromethyl-dimethoxy-methyl silane

C-chloromethyl-diethoxy-methyl silane

D-chloromethyl-diisopropoxy-methyl silane

E-alpha-chloroethyl-dimethoxy-methyl silane

    ______________________________________                                        Compound                                                                      No.      Olive-Fall (%)                                                                             Compound   Olive-fall (%)                               ______________________________________                                        untreated                                                                     control   2%          D           5%                                          A         2%          E          10%                                          B         2%          6          99%                                          C         3%          8          96%                                          10       55%          54         29%                                          15       90%          55         36%                                          17       85%          56         81%                                          18       94%          58         30%                                          19       90%          59         60%                                          20       90%          60         52%                                          21       72%          61         74%                                          22       80%          63         28%                                          23       60%          65         26%                                          24       95%          68         88%                                          25       95%          70         33%                                          26       83%          71         80%                                          28       51%          73         25%                                          29       36%          74         34%                                          30       70%          76         38%                                          31       52%          77         98%                                          32       99%          80         48%                                          33       78%          83         38%                                          36       28%          85         31%                                          37       48%          87         66%                                          41       43%          88         34%                                          43       80%          89         41%                                          44       72%          91         41%                                          45       90%          93         30%                                          46       62%          96         44%                                          47       70%          98         42%                                          48       95%          102        43%                                          49       55%          107        24%                                          50       28%          108        28%                                          52       33%          123        33%                                          124      82%                                                                  125      73%                                                                  127      100%                                                                 129      29%                                                                  130      42%                                                                  131      64%                                                                  132      55%                                                                  133      46%                                                                  134      97%                                                                  135      96%                                                                  ______________________________________                                    

The data presented hereinabove clearly illustrates the excellent growthregulatory performance characteristics of the compounds of thisinvention. Furthermore, it establishes a distinct pattern of superiorperformance over the prior art Leasure compounds.

What is claimed is:
 1. A composition for facilitating fruit abscissing,fruit thinning and fruit ripening which comprises an effective amount ofa compound corresponding to the formula ##STR27## wherein X is chlorineor bromine, Y represents the radical --OR₃ and each of R₁, R₂ and R₃ islower alkoxyalkyl, together with a suitable inert carrier therefor.
 2. Amethod for regulating the growth of plants as to facilitate fruitabscission, fruit thinning and fruit ripening which comprises applyingto said plants an effective growth-regulating amount of a compoundaccording to the formula of claim
 1. 3. The method of claim 2, whereinR₁, R₂ and R₃ are 2-methoxyethyl.
 4. The method of claim 2, wherein R₁,R₂ and R₃ are 2-ethoxyethyl.
 5. The method of claim 2, wherein R₁, R₂and R₃ are 2-butoxyethyl.
 6. The method of claim 2, wherein said growthregulation is directed to the abscission of fruit.
 7. The method ofclaim 2, wherein said growth regulation is directed to the acceleratedripening of fruit.
 8. The method of claim 2, wherein said growthregulation is directed to the thinning of fruits.